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Potassium Acetate-Catalyzed Double Decarboxylative Transannulation To Access Highly Functionalized Pyrroles

Jun‐Kuan Li, Biying Zhou, Yuchen Tian, Chunman Jia, Xiao‐Song Xue, Fa‐Guang Zhang, Jun‐An Ma

2020Organic Letters21 citationsDOI

Abstract

The development of new synthetic strategies for the efficient construction of versatile pyrrole pharmacores, especially in an operationally simple and environmentally benign fashion, still remains a momentous yet challenging goal. Here, we report a KOAc-catalyzed double decarboxylative transannulation between readily accessible oxazolones and isoxazolidinediones. This transformation represents a new way for skeletal remodeling by utilizing CO2 moiety as traceless activating and directing groups in both reaction partners. The synthetic value is evidenced by the rapid preparation of a broad spectrum of highly functionalized 3-carbamoyl-4-aryl pyrroles in good to excellent yields with exclusive regio-control, including the important Atorvastatin core.

Topics & Concepts

ChemistryMoietyCombinatorial chemistryCatalysisArylBroad spectrumAromatizationPyrroleDecarboxylationOrganic chemistryAlkylSynthesis and Characterization of PyrrolesCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods